Sodium hydride → trans-Methyl 2-(3-chloro-2-methylphenyl)cyclopropanecarboxylate

HRID 2175312노트

반응식

HRID 2175312 반응식
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[Cl:9][C:10]1[C:11]([CH3:22])=[C:12](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][CH:15]=1>CS(C)=O>[Cl:9][C:10]1[C:11]([CH3:22])=[C:12]([C@@H:16]2[CH2:2][C@H:17]2[C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86712608(E)-Methyl 3-(3-chloro-2-methylphenyl)acrylate

생성물 1

HCID 70981958trans-Methyl 2-(3-chloro-2-methylphenyl)cyclopropanecarboxylate수율 39.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To a solution of trimethylsulfoxonium iodide (0.157 g, 0.712 mmol) in 1 mL DMSO was added NaH (60% in mineral oil) (0.032 g, 0.807 mmol) portion-wise. The mixture was stirred at room temperature for 30 min, and then a solution (E)-methyl 3-(3-chloro-2-methylphenyl)acrylate (0.1 g, 0.475 mmol) in 1 mL DMSO was added in one portion. The reaction was stirred at room temperature for 16 h. The mixture was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried (MgSO4) and concentrated. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (0.042 g, 39% yield) as a clear colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.29-7.24 (d, J=7.8 Hz, 1H), 7.06 (t, J=7.8 Hz, 1H), 6.95 (d, J=7.7 Hz, 1H), 3.79-3.75 (m, 3H), 2.55 (ddd, J=9.1, 6.7, 4.5 Hz, 1H), 2.45 (s, 3H), 1.81 (dt, J=8.4, 4.9 Hz, 1H), 1.64-1.57 (m, 1H), 1.30 (ddd, J=8.4, 6.7, 4.4 Hz, 1H).

후처리

  1. stirringThe reaction was stirred at room temperature for 16 h
  2. customThe mixture was partitioned between EtOAc and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-37e46d9f8c874032a3f8ad46b99e1574
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062028B2

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